Why Freelancers Don’t Have It As Easy As You Think

Kyle RackiMay 06, 2014
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5 min. read

To regular people on a payroll who get to complain about bosses, co-workers, and severe cases of the Mondays, a freelancer must seem like a strange fantastical character straight out of Tolkien, perhaps how Strider first appeared to the hobbits in Fellowship; a vagrant wandering the wilderness in search of enemies, adventure and only the finest brew pubs.

At first, the Shire-folk didn’t understand Strider’s freewheeling lifestyle, but when they observed first-hand his sword-wielding, ringwraith-punking, Liv-Tyler-scoring abilities, they were like, “Yeah, he’s a pretty cool dude”.

And that’s how most agency people view freelancers, they’re like the Kramers of the marketing world, dating supermodels and running Kramerica without ever leaving their apartment. But being a freelancer isn’t all sunshine and free cereal. Here are some of the challenges they face on a daily basis.

No structure and constant distractions

As a freelancer, there’s very little stopping you from going to bed each night. Just a bit more work on that project. Just need to finish up clearing the ol’ inbox. Just one more video of a dead whale exploding (remember, Youtube gets weirder the later at night it gets). By the time you get to sleep it’s 3:30 am.

Now it’s 9 am. You know you should get up, but you don’t feel like it. And why should you? There’s no boss waiting to give you dirty looks when you show up late. There’s no projects due this very minute. So who’s to say you shouldn’t hit snooze one more time and curl back up into your sweet cocoon of shame?

By the time you make coffee, check your blog feed, and start rolling up your sleeves you hear the noontime cannon going off and realize, “I just opened Photoshop.”

Now you have to work late to make up for all the time you wasted, the entire morning your inbox was filling up with emails that you’ll have to clear before you cap the evening off with more Youtube videos you hope you'll never have to explain to anyone, and eventually you remember you haven’t showered in days. Sound fun?

They don’t socialize like the rest of us

Hopefully you like all the people you work with, or least some of them. Two of them? Even if you only like two people you work with, every day you go to the office is like a day spent with friends, and that makes it feel a bit less like work.

You can play light-hearted pranks on each other, like taking a stack of your co-workers business cards and meticulously hiding them in every nook and cranny of his desk area so he’s still finding business cards to this day. I did that to a copywriter once.

You can also draw caricatures of your colleagues, like when I drew a fellow designer, named Chad, every day for the two years I worked there. Eventually I had a stack of hundreds of Chad sketches in various situations and costumes. There was Chad as a scuba diver, Chad as a knight, Chad as a weatherman reporting on a hurricane and Chad as an actual hurricane. For the week of halloween even drew Chad as different monsters labelled with names like Count Chadula and Chombie.

My point is, we had fun. Or at least everyone except Chad did.

Freelancers don’t get that kind of frat-like work environment to fill each day with. “But I go to my favourite coffee house and have a good chat with my barista”, they’ll argue in a sad, whimpering voice. It doesn’t matter. They’re alone and they know it.

Your family doesn’t understand

If a freelancer has kids, forget it. You think you get interrupted at the office? Try having a six-year old knocking on your door once on the hour to see if you’re done work yet. Here’s the conversation I usually have with my son:

“Daddy, are you done work soon?”

“Micah, I don’t know, I’m busy. Please don’t come in anymore.”

Five minutes later…

“Daddy, I know you said not to come in, but I have to tell you something important: I need some help fighting Bane in Arkham. I’m not asking you to play the game, I’m just asking if you’ll tell me what to do.”

5 minutes later

All the ways you should be using your freedom but aren't

When you dream about going freelance, what do you think of? Working from a café somewhere in Italy, downing shot after shot of espresso while a moustachioed barista tells you ‘you’re-a his favorite-a custama”? Killing time between rounds of client changes by surfing in South Africa, occasionally high-fiving a school of passing sharks?

Freelance is wrapped up in the idea of true freedom - freedom to live the lifestyle of your dreams by living and working anywhere in the world. But too often, freelancers are victims of their own success, never taking a vacation, constantly bogged down in too much work and never having the confidence to say no to a new client project.

Eventually, they start to envy salaried employees, what with their steady pay checks and paid vacation. In time, they may even quit their freelance practice to rejoin the ranks of an agency team, almost as if Strider were to suddenly leave the wandering bad-ass ranger lifestyle to follow Frodo and the gang back to the Shire.

Middle-earth may be doomed, but at least he remembers the taste of strawberries.